Three of Apple Music's most integral executives sit down to speak about Drake and the ambitions of their revolutionary streaming service.

Fifteen years ago, Apple changed the music industry. Everyone remembers the launch of the iPod and the iTunes store and its earth-shattering wake: the MP3 revolution, thousands of songs in your pocket, the decimation of the music industry as we knew it. Now, with the rise of streaming, the industry is standing at the precipice of another sea change. Once again, Apple is telling the world that it’s going to transform how you listen to music.

Eighteen months after its debut, Apple Music is clearly more than just a streaming service. Any assumptions that Apple was taking on Spotify, Tidal, and their ilk, by simply making a splashy clone and putting it on every iPhone on Earth have been dispelled. Instead, Apple Music is trying to do, well, everything. Under the guidance of its head of content, Larry Jackson, 35, it’s signing the biggest names in music—including Drake, Frank Ocean, and Taylor Swift—to exclusive deals, and flying right in the face of the old-world labels to do so. Apple has established its own radio station, Beats 1, and poached Zane Lowe, 43, from BBC Radio 1 to serve as its leading personality. And it has Bozoma Saint John, 39, who ran music and entertainment marketing at Pepsi and reportedly brokered Beyoncé’s 2013 Super Bowl performance, to explain what Apple Music is for the masses who have never shelled out for a streaming subscription.

If Apple Music seems freewheeling, that’s because it is. It’s laying out a future for the music industry, but right now, the path ahead is murky. The company is seemingly figuring things out as it goes—a far cry, metaphorically speaking, from the perfectly designed rectangle of the iPod. Unlike Steve Jobs, Jackson, Lowe, and Saint John aren’t designers—they’re plucked directly from the entertainment industry. Fittingly, it’s a new kind of leadership for the next chapter of music history.

It’s been almost 18 months since Apple Music’s launch, and it isn’t a simple streaming platform anymore. How would each of you describe Apple Music today?
Larry Jackson:It’s really interesting that you would even ask a question like that, because it means that we’ve achieved what we set out to achieve initially: Make something that’s the intersection of all things pop-culture. To make it more than just a utility. I like to think of it as a place where the best creative thinkers in music can congregate and come up with different ideas.Zane Lowe: Larry was the first person who ever called me and asked if I wanted to be involved in Apple Music. For the most part, it remains how he and I talked about it in that first conversation, which was a place for music to live, and for artists to call home, and for an audience to feel like this is where the conversation is happening. I want it to go deeper than just availability.Bozoma Saint John: Apple Music is a living, breathing brand. Obviously, as a marketer, I love to work with brands that aren’t static, that have life and personality. Apple Music has that. It’s very affirming to be able to take the personalities that already exist and then make that one statement that can move culture.

"I would hate to be on the outside of this room right now." —zane Lowe

Did you have trouble convincing people to get on board?Jackson:Before the product launched, a lot of it felt like we were trying to explain something that was science fiction.Saint John: Absolutely. We created presentations to explain what this was. It was like the famous Today show, when they’re like, “Tell us about the Internet. What is this Internet?” Lowe: Some people got it straight away. Elton John, David Furnish, Pharrell Williams were just like, “Yep.” Do you remember when we had dinner with Drake? He got it quick. Other people needed a lot more finessing. Trying to work out what our personality is, and how to define what Apple Music is going to be, that’s been happening in front of people. Starting something from scratch, even though it’s the most challenging time, is a once-in-a-lifetime opportunity.

Image via Complex Original

What have you learned since the launch?Jackson: I’ve learned the art of the pivot, learning quickly what doesn’t work. It’s very difficult to be, as a company or just as a person, all things to everyone. Lowe:If you are deeply serious about music and follow how it evolves, and how it moves into a new era, [you know that] we’re in the middle of that shift. Every day something is changing or moving or evolving for people who love music and entertainment. This is how they will consume it. They will go, “I get that for news, I get that for entertainment, I get that for magazines, I get that for movies, and I get that for music.” We’re lining it up, and it’s building to a tipping point over time. I don’t want to speak for these two very talented people here with me, but I think I can: We’re all pretty impatient.Saint John: And perfectionists, to some degree.Lowe: We all want it to be really good, right now, just for music’s sake. We’re all still working it out, and even when you don’t have the answer, it’s still a privilege to be in the conversation. I would hate to be on the outside of this room right now.

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What are the advantages and disadvantages of working on this project at a company like Apple?Saint John:Apple is a unique company, in that the art and the science sit together very nicely. There’s an appreciation for both sides of the brain. For me, it’s a much easier conversation in this particular environment, because you have to appreciate what is a very artistic, emotional, ever-changing platform, and also have the rigor of a technology that cannot fail, that has to be consistent. It doesn’t have any flexibility.Lowe:With tech, it’s mathematics. There are hard margins. What happens when you take something that you love, that makes you feel a certain way, that’s made of those hard margins? What does the future feel and sound like? How do you keep the humanity and the feelings and the stories and the conversations in it? Jackson: My role, on a spiritual level, is to bring the best out of people. When we did [Please Forgive Me, Drake’s 20-minute music video, which Jackson co-wrote] in particular, that was in South Africa, and it was really difficult for Drake. He’s at the height of everything for, like, six weeks, and uprooted his life to go to Africa for seven days in the middle of BET [Awards] week, when he’s nominated for more awards than anybody. All for an idea that we had. Lowe: I remember calling you up and you were the most stressed out I’ve ever heard you. Jackson: Yeah, it was bringing out the best in us at the time. Everything we’re doing here is truly a collaboration with artists. We can’t take credit for the work. Taylor Swift came in with a great idea earlier this year [for her 1989 World Tour documentary]. It’s just collaborating in a really beautiful sense.Lowe: We had that with Drake and Future, with What a Time to Be Alive. I was at your house when Drake played that mixtape out, on OVO Sound twice, and we were just freaking out. Do you remember?Jackson: Of course, yeah.Lowe: It was shutting everything down. You could feel the energy of the world, for Drake fans, centering around devices, listening to this moment, proving the fact that you can still have a community experience [in music]. You can still have a moment for people. You can still bring people together. Saint John: And I provide the microphone, and the megaphone. There’s a point of discovery about Apple Music that is so key to all of this, right? But if we don’t tell people how to get to us, or what is happening, then it’s impossible with all of the noise. I’m going to tell the whole world, “Hey! Pay attention, right here. The party’s over here, guys!” I’m like the promoter. I’m out here handing out fliers on the street, like, “Yo, come to the party.”

What do you want the music industry to look like in five or 10 years?Saint John: We’re developing something very special and we just want people to pay attention to it. My five-year vision is that I want every single person on the planet to be engaged on Apple Music. I truly believe we’ve created something very, very special. I don’t think anyone else can do this. I will scream from the mountain top until everyone knows. Can I add one thing, too? This is a love fest right now, but I also feel like our conflict makes us better, too. There’s plenty of times where I have screamed at Larry. And though he has not screamed back, I have felt his frustration.Lowe: Has he ever lost it with you?Saint John:No. Never.Lowe:[To Jackson] We did have one conversation where you got frustrated, do you remember?Jackson: Yeah. And then I got on a plane and went to London.Saint John:[To Jackson]You always keep your cool. But the conflict has also made us better, right? I can get really frustrated.Lowe: Because it’s stressful when you’re trying to come up with something new that fills something that’s missing in people’s lives.Saint John: And we’re all so passionate about it. There has to be conflict. It makes the experience that much richer, even when we don’t come to an agreement.Jackson: The conflict is a secret sauce.

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